Preparative deracemization of unnatural amino acids

Fotheringham, I, Archer, I, Carr, R, Speight, R and Turner, NJ (2006) Preparative deracemization of unnatural amino acids. Biochemical Society Transactions, 34 2: 287-290. doi:10.1042/BST20060287

Author Fotheringham, I
Archer, I
Carr, R
Speight, R
Turner, NJ
Title Preparative deracemization of unnatural amino acids
Journal name Biochemical Society Transactions   Check publisher's open access policy
ISSN 0300-5127
Publication date 2006-04-01
Year available 2006
Sub-type Article (original research)
DOI 10.1042/BST20060287
Open Access Status Not Open Access
Volume 34
Issue 2
Start page 287
End page 290
Total pages 4
Place of publication London, United Kingdom
Publisher Portland Press Ltd.
Language eng
Formatted abstract
Unnatural amino acids are a growing class of intermediates required for pharmaceuticals, agrochemicals and other industrial products. However, no single method has proven sufficiently versatile to prepare these compounds broadly at scale. To address this need, we have developed a general chemoenzymatic process to prepare enantiomerically pure L- and D-amino acids in high yield by deracemization of racemic starting materials. This method involves the concerted action of an enantioselective oxidase biocatalyst and a non-selective chemical reducing agent to effect the stereoinversion of one enantiomer and can result in an enantiomeric excess of >99% from the starting racemate, and product yields of over 90%. This approach compares very favourably with resolution processes, which have a maximum single-pass yield of 50%. We have developed efficient methods to adapt the process towards new target compounds and to optimize key factors that influence process efficiency and offer competitive economics at scale
Keyword Biocatalysis
Chiral amine
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Australian Institute for Bioengineering and Nanotechnology Publications
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Citation counts: TR Web of Science Citation Count  Cited 25 times in Thomson Reuters Web of Science Article | Citations
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Created: Thu, 12 Sep 2013, 19:24:16 EST by Cathy Fouhy on behalf of Aust Institute for Bioengineering & Nanotechnology